diff --git a/.bazelrc b/.bazelrc
index d7e1771336..801b963ad5 100644
--- a/.bazelrc
+++ b/.bazelrc
@@ -16,6 +16,7 @@ test --test_output=errors
 # creating (possibly empty) __init__.py files and adding them to the srcs of
 # Python targets as required.
 build --incompatible_default_to_explicit_init_py
+build --//python/config_settings:incompatible_default_to_explicit_init_py=True
 
 # Ensure ongoing compatibility with this flag.
 common --incompatible_disallow_struct_provider_syntax
diff --git a/CHANGELOG.md b/CHANGELOG.md
index d7c480582a..4f9ac020d7 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -85,6 +85,8 @@ END_UNRELEASED_TEMPLATE
   evaluated, see [our docs](/pypi/download.html#customizing-requires-dist-resolution) on customizing `Requires-Dist` resolution.
 * (toolchains) Added Python versions 3.14.0, 3.13.8, 3.12.12, 3.11.14, 3.10.19, and 3.9.24
   from the [20251010] release.
+* (deps) (bzlmod) Upgraded to `bazel-skylib` version
+  [1.8.2](https://github.com/bazelbuild/bazel-skylib/releases/tag/1.8.2)
 
 [20251010]: https://github.com/astral-sh/python-build-standalone/releases/tag/20251010
 
diff --git a/MODULE.bazel b/MODULE.bazel
index 36135bbb8b..5854595bed 100644
--- a/MODULE.bazel
+++ b/MODULE.bazel
@@ -5,7 +5,7 @@ module(
 )
 
 bazel_dep(name = "bazel_features", version = "1.21.0")
-bazel_dep(name = "bazel_skylib", version = "1.8.1")
+bazel_dep(name = "bazel_skylib", version = "1.8.2")
 bazel_dep(name = "rules_cc", version = "0.1.5")
 bazel_dep(name = "platforms", version = "0.0.11")
 
diff --git a/docs/api/rules_python/python/config_settings/index.md b/docs/api/rules_python/python/config_settings/index.md
index 989ebf1128..78a74c3f37 100644
--- a/docs/api/rules_python/python/config_settings/index.md
+++ b/docs/api/rules_python/python/config_settings/index.md
@@ -24,6 +24,65 @@ This is a transition flag and will be removed in a subsequent release.
 ::::
 :::
 
+::::{bzl:flag} build_python_zip
+Controls if a `py_binary/py_test` output is a self-executable zipapp.
+
+When enabled, the output of `py_binary` or `py_test` targets will be a
+self-executable zipapp.
+
+:::{note}
+This affects _all_ `py_binary` and `py_test` targets in the build, not
+only the target(s) specified on the command line.
+:::
+
+Values:
+* `true`
+* `false`
+
+This flag replaces the Bazel builtin `--build_python_zip` flag.
+
+:::{versionadded} VERSION_NEXT_FEATURE
+:::
+::::
+
+::::{bzl:flag} experimental_python_import_all_repositories
+Controls whether repository directories are added to the import path.
+
+When enabled, the top-level directories in the runfiles root directory (which
+are presumbed to be repository directories) are added to the Python import
+search path.
+
+It's recommended to set this to **`false`** to avoid external dependencies
+unexpectedly interferring with import searching.
+
+Values;
+* `true` (default)
+* `false`
+
+This flag replaces the Bazel builtin
+`--experimental_python_import_all_repositories` flag.
+
+:::{versionadded} VERSION_NEXT_FEATURE
+:::
+::::
+
+::::{bzl:flag} python_path
+A fallback path to use for Python for particular legacy Windows-specific code paths.
+
+Deprecated, do not use. This flag is largely a no-op and was replaced by
+toolchains. It only remains for some legacy Windows code-paths that will
+be removed.
+
+This flag replaces the Bazel builtin `--python_path` flag.
+
+:::{deprecated} VERSION_NEXT_FEATURE
+Use toolchains instead.
+:::
+
+:::{versionadded} VERSION_NEXT_FEATURE
+:::
+::::
+
 :::{bzl:flag} python_version
 Determines the default hermetic Python toolchain version. This can be set to
 one of the values that `rules_python` maintains.
@@ -33,6 +92,29 @@ one of the values that `rules_python` maintains.
 Parses the value of the `python_version` and transforms it into a `X.Y` value.
 :::
 
+::::{bzl:flag} incompatible_default_to_explicit_init_py
+Controls if missing `__init__.py` files are generated or not.
+
+If false, `py_binary` and `py_test` will, for every `*.py` and `*.so` file,
+create `__init__.py` files for the containing directory, and all parent
+directories, that do not already have an `__init__.py` file. If true, this
+behavior is disabled.
+
+It's recommended to disable this behavior to avoid surprising import effects
+from directories being importable when they otherwise wouldn't be, and for
+how it can interfere with implicit namespace packages.
+
+Values:
+* `true`: do not generate missing `__init__.py` files
+* `false` (default): generate missing `__init__.py` files
+
+This flag replaces the Bazel builtin
+`--incompatible_default_to_explicit_init_py` flag.
+
+:::{versionadded} VERSION_NEXT_FEATURE
+:::
+::::
+
 :::{bzl:target} is_python_*
 config_settings to match Python versions
 
diff --git a/examples/build_file_generation/WORKSPACE b/examples/build_file_generation/WORKSPACE
index 27f6ec071c..27d0d13b7c 100644
--- a/examples/build_file_generation/WORKSPACE
+++ b/examples/build_file_generation/WORKSPACE
@@ -7,54 +7,7 @@ workspace(name = "build_file_generation_example")
 # file.  When the symbol is loaded you can use the rule.
 load("@bazel_tools//tools/build_defs/repo:http.bzl", "http_archive")
 
-######################################################################
-# We need rules_go and bazel_gazelle, to build the gazelle plugin from source.
-# Setup instructions for this section are at
-# https://github.com/bazelbuild/bazel-gazelle#running-gazelle-with-bazel
-# You may need to update the version of the rule, which is listed in the above
-# documentation.
-######################################################################
-
-# Define an http_archive rule that will download the below ruleset,
-# test the sha, and extract the ruleset to you local bazel cache.
-
-http_archive(
-    name = "io_bazel_rules_go",
-    sha256 = "9d72f7b8904128afb98d46bbef82ad7223ec9ff3718d419afb355fddd9f9484a",
-    urls = [
-        "https://mirror.bazel.build/github.com/bazel-contrib/rules_go/releases/download/v0.55.1/rules_go-v0.55.1.zip",
-        "https://github.com/bazel-contrib/rules_go/releases/download/v0.55.1/rules_go-v0.55.1.zip",
-    ],
-)
-
-# Download the bazel_gazelle ruleset.
-http_archive(
-    name = "bazel_gazelle",
-    sha256 = "75df288c4b31c81eb50f51e2e14f4763cb7548daae126817247064637fd9ea62",
-    urls = [
-        "https://mirror.bazel.build/github.com/bazelbuild/bazel-gazelle/releases/download/v0.36.0/bazel-gazelle-v0.36.0.tar.gz",
-        "https://github.com/bazelbuild/bazel-gazelle/releases/download/v0.36.0/bazel-gazelle-v0.36.0.tar.gz",
-    ],
-)
-
-# Load rules_go ruleset and expose the toolchain and dep rules.
-load("@bazel_gazelle//:deps.bzl", "gazelle_dependencies")
-load("@io_bazel_rules_go//go:deps.bzl", "go_register_toolchains", "go_rules_dependencies")
-
-# go_rules_dependencies is a function that registers external dependencies
-# needed by the Go rules.
-# See: https://github.com/bazelbuild/rules_go/blob/master/go/dependencies.rst#go_rules_dependencies
-go_rules_dependencies()
-
-# go_rules_dependencies is a function that registers external dependencies
-# needed by the Go rules.
-# See: https://github.com/bazelbuild/rules_go/blob/master/go/dependencies.rst#go_rules_dependencies
-go_register_toolchains(version = "1.21.13")
-
-# The following call configured the gazelle dependencies, Go environment and Go SDK.
-gazelle_dependencies()
-
-# Remaining setup is for rules_python.
+# Setup rules_python.
 
 # DON'T COPY_PASTE THIS.
 # Our example uses `local_repository` to point to the HEAD version of rules_python.
@@ -124,6 +77,53 @@ load("@pip//:requirements.bzl", "install_deps")
 # Initialize repositories for all packages in requirements_lock.txt.
 install_deps()
 
+######################################################################
+# We need rules_go and bazel_gazelle, to build the gazelle plugin from source.
+# Setup instructions for this section are at
+# https://github.com/bazelbuild/bazel-gazelle#running-gazelle-with-bazel
+# You may need to update the version of the rule, which is listed in the above
+# documentation.
+######################################################################
+
+# Define an http_archive rule that will download the below ruleset,
+# test the sha, and extract the ruleset to you local bazel cache.
+
+http_archive(
+    name = "io_bazel_rules_go",
+    sha256 = "9d72f7b8904128afb98d46bbef82ad7223ec9ff3718d419afb355fddd9f9484a",
+    urls = [
+        "https://mirror.bazel.build/github.com/bazel-contrib/rules_go/releases/download/v0.55.1/rules_go-v0.55.1.zip",
+        "https://github.com/bazel-contrib/rules_go/releases/download/v0.55.1/rules_go-v0.55.1.zip",
+    ],
+)
+
+# Download the bazel_gazelle ruleset.
+http_archive(
+    name = "bazel_gazelle",
+    sha256 = "75df288c4b31c81eb50f51e2e14f4763cb7548daae126817247064637fd9ea62",
+    urls = [
+        "https://mirror.bazel.build/github.com/bazelbuild/bazel-gazelle/releases/download/v0.36.0/bazel-gazelle-v0.36.0.tar.gz",
+        "https://github.com/bazelbuild/bazel-gazelle/releases/download/v0.36.0/bazel-gazelle-v0.36.0.tar.gz",
+    ],
+)
+
+# Load rules_go ruleset and expose the toolchain and dep rules.
+load("@bazel_gazelle//:deps.bzl", "gazelle_dependencies")
+load("@io_bazel_rules_go//go:deps.bzl", "go_register_toolchains", "go_rules_dependencies")
+
+# go_rules_dependencies is a function that registers external dependencies
+# needed by the Go rules.
+# See: https://github.com/bazelbuild/rules_go/blob/master/go/dependencies.rst#go_rules_dependencies
+go_rules_dependencies()
+
+# go_rules_dependencies is a function that registers external dependencies
+# needed by the Go rules.
+# See: https://github.com/bazelbuild/rules_go/blob/master/go/dependencies.rst#go_rules_dependencies
+go_register_toolchains(version = "1.21.13")
+
+# The following call configured the gazelle dependencies, Go environment and Go SDK.
+gazelle_dependencies()
+
 # The rules_python gazelle extension has some third-party go dependencies
 # which we need to fetch in order to compile it.
 load("@rules_python_gazelle_plugin//:deps.bzl", _py_gazelle_deps = "gazelle_deps")
diff --git a/gazelle/.bazelrc b/gazelle/.bazelrc
index 97040903a6..791b93912a 100644
--- a/gazelle/.bazelrc
+++ b/gazelle/.bazelrc
@@ -7,6 +7,7 @@ test --test_output=errors
 # creating (possibly empty) __init__.py files and adding them to the srcs of
 # Python targets as required.
 build --incompatible_default_to_explicit_init_py
+build --@rules_python//python/config_settings:incompatible_default_to_explicit_init_py=True
 
 # Windows makes use of runfiles for some rules
 build --enable_runfiles
diff --git a/gazelle/MODULE.bazel b/gazelle/MODULE.bazel
index 1560e73d7b..add5986903 100644
--- a/gazelle/MODULE.bazel
+++ b/gazelle/MODULE.bazel
@@ -4,7 +4,7 @@ module(
     compatibility_level = 1,
 )
 
-bazel_dep(name = "bazel_skylib", version = "1.6.1")
+bazel_dep(name = "bazel_skylib", version = "1.8.2")
 bazel_dep(name = "rules_python", version = "0.18.0")
 bazel_dep(name = "rules_go", version = "0.55.1", repo_name = "io_bazel_rules_go")
 bazel_dep(name = "gazelle", version = "0.36.0", repo_name = "bazel_gazelle")
diff --git a/gazelle/WORKSPACE b/gazelle/WORKSPACE
index ec0532c3f6..f4a3abf36c 100644
--- a/gazelle/WORKSPACE
+++ b/gazelle/WORKSPACE
@@ -2,6 +2,19 @@ workspace(name = "rules_python_gazelle_plugin")
 
 load("@bazel_tools//tools/build_defs/repo:http.bzl", "http_archive")
 
+http_archive(
+    name = "bazel_skylib",
+    sha256 = "6e78f0e57de26801f6f564fa7c4a48dc8b36873e416257a92bbb0937eeac8446",
+    urls = [
+        "https://mirror.bazel.build/github.com/bazelbuild/bazel-skylib/releases/download/1.8.2/bazel-skylib-1.8.2.tar.gz",
+        "https://github.com/bazelbuild/bazel-skylib/releases/download/1.8.2/bazel-skylib-1.8.2.tar.gz",
+    ],
+)
+
+load("@bazel_skylib//:workspace.bzl", "bazel_skylib_workspace")
+
+bazel_skylib_workspace()
+
 http_archive(
     name = "io_bazel_rules_go",
     sha256 = "9d72f7b8904128afb98d46bbef82ad7223ec9ff3718d419afb355fddd9f9484a",
diff --git a/internal_dev_deps.bzl b/internal_dev_deps.bzl
index 91f5defd3e..811240a06a 100644
--- a/internal_dev_deps.bzl
+++ b/internal_dev_deps.bzl
@@ -60,10 +60,10 @@ def rules_python_internal_deps():
 
     http_archive(
         name = "bazel_skylib",
-        sha256 = "bc283cdfcd526a52c3201279cda4bc298652efa898b10b4db0837dc51652756f",
+        sha256 = "6e78f0e57de26801f6f564fa7c4a48dc8b36873e416257a92bbb0937eeac8446",
         urls = [
-            "https://mirror.bazel.build/github.com/bazelbuild/bazel-skylib/releases/download/1.7.1/bazel-skylib-1.7.1.tar.gz",
-            "https://github.com/bazelbuild/bazel-skylib/releases/download/1.7.1/bazel-skylib-1.7.1.tar.gz",
+            "https://mirror.bazel.build/github.com/bazelbuild/bazel-skylib/releases/download/1.8.2/bazel-skylib-1.8.2.tar.gz",
+            "https://github.com/bazelbuild/bazel-skylib/releases/download/1.8.2/bazel-skylib-1.8.2.tar.gz",
         ],
     )
 
diff --git a/python/config_settings/BUILD.bazel b/python/config_settings/BUILD.bazel
index cc5c472fe7..369989eb1e 100644
--- a/python/config_settings/BUILD.bazel
+++ b/python/config_settings/BUILD.bazel
@@ -1,5 +1,6 @@
 load("@bazel_skylib//rules:common_settings.bzl", "bool_flag", "string_flag")
 load("@pythons_hub//:versions.bzl", "DEFAULT_PYTHON_VERSION", "MINOR_MAPPING", "PYTHON_VERSIONS")
+load("@rules_python_internal//:rules_python_config.bzl", "config")
 load(
     "//python/private:flags.bzl",
     "AddSrcsToRunfilesFlag",
@@ -244,5 +245,28 @@ label_flag(
 bool_flag(
     name = "experimental_python_import_all_repositories",
     build_setting_default = True,
+    scope = "universal",
+    visibility = ["//visibility:public"],
+)
+
+bool_flag(
+    name = "build_python_zip",
+    build_setting_default = config.build_python_zip_default,
+    help = "Build python executable zip. Defaults to on on Windows, off on other platforms",
+    scope = "universal",
+    visibility = ["//visibility:public"],
+)
+
+bool_flag(
+    name = "incompatible_default_to_explicit_init_py",
+    build_setting_default = False,
+    scope = "universal",
+    visibility = ["//visibility:public"],
+)
+
+string_flag(
+    name = "python_path",
+    build_setting_default = "python",
+    scope = "universal",
     visibility = ["//visibility:public"],
 )
diff --git a/python/private/common_labels.bzl b/python/private/common_labels.bzl
index 4a6f6d3f0f..e90679eb6f 100644
--- a/python/private/common_labels.bzl
+++ b/python/private/common_labels.bzl
@@ -7,6 +7,7 @@ labels = struct(
     # keep sorted
     ADD_SRCS_TO_RUNFILES = str(Label("//python/config_settings:add_srcs_to_runfiles")),
     BOOTSTRAP_IMPL = str(Label("//python/config_settings:bootstrap_impl")),
+    BUILD_PYTHON_ZIP = str(Label("//python/config_settings:build_python_zip")),
     EXEC_TOOLS_TOOLCHAIN = str(Label("//python/config_settings:exec_tools_toolchain")),
     PIP_ENV_MARKER_CONFIG = str(Label("//python/config_settings:pip_env_marker_config")),
     NONE = str(Label("//python:none")),
@@ -18,6 +19,7 @@ labels = struct(
     PRECOMPILE = str(Label("//python/config_settings:precompile")),
     PRECOMPILE_SOURCE_RETENTION = str(Label("//python/config_settings:precompile_source_retention")),
     PYC_COLLECTION = str(Label("//python/config_settings:pyc_collection")),
+    PYTHON_IMPORT_ALL_REPOSITORIES = str(Label("//python/config_settings:experimental_python_import_all_repositories")),
     PYTHON_SRC = str(Label("//python/bin:python_src")),
     PYTHON_VERSION = str(Label("//python/config_settings:python_version")),
     PYTHON_VERSION_MAJOR_MINOR = str(Label("//python/config_settings:python_version_major_minor")),
diff --git a/python/private/flags.bzl b/python/private/flags.bzl
index 35181e9f96..d9e3aa41c3 100644
--- a/python/private/flags.bzl
+++ b/python/private/flags.bzl
@@ -71,7 +71,7 @@ def read_possibly_native_flag(ctx, flag_name):
         return _POSSIBLY_NATIVE_FLAGS[flag_name][0](ctx)
     else:
         # Starlark definition of "--foo" is assumed to be a label dependency named "_foo".
-        return getattr(ctx.attr, "_" + flag_name)[BuildSettingInfo].value
+        return getattr(ctx.attr, "_" + flag_name + "_flag")[BuildSettingInfo].value
 
 def _AddSrcsToRunfilesFlag_is_enabled(ctx):
     value = ctx.attr._add_srcs_to_runfiles_flag[BuildSettingInfo].value
diff --git a/python/private/internal_config_repo.bzl b/python/private/internal_config_repo.bzl
index 0c6210696e..dac6d741a5 100644
--- a/python/private/internal_config_repo.bzl
+++ b/python/private/internal_config_repo.bzl
@@ -28,6 +28,7 @@ _ENABLE_DEPRECATION_WARNINGS_DEFAULT = "0"
 
 _CONFIG_TEMPLATE = """
 config = struct(
+  build_python_zip_default = {build_python_zip_default},
   enable_pystar = True,
   enable_pipstar = {enable_pipstar},
   enable_deprecation_warnings = {enable_deprecation_warnings},
@@ -96,6 +97,7 @@ def _internal_config_repo_impl(rctx):
         builtin_py_cc_link_params_provider = "PyCcLinkParamsProvider"
 
     rctx.file("rules_python_config.bzl", _CONFIG_TEMPLATE.format(
+        build_python_zip_default = repo_utils.get_platforms_os_name(rctx) == "windows",
         enable_pipstar = _bool_from_environ(rctx, _ENABLE_PIPSTAR_ENVVAR_NAME, _ENABLE_PIPSTAR_DEFAULT),
         enable_deprecation_warnings = _bool_from_environ(rctx, _ENABLE_DEPRECATION_WARNINGS_ENVVAR_NAME, _ENABLE_DEPRECATION_WARNINGS_DEFAULT),
         builtin_py_info_symbol = builtin_py_info_symbol,
diff --git a/python/private/py_executable.bzl b/python/private/py_executable.bzl
index ad1afa91cd..1a5ad4c3c6 100644
--- a/python/private/py_executable.bzl
+++ b/python/private/py_executable.bzl
@@ -77,6 +77,13 @@ EXECUTABLE_ATTRS = dicts.add(
     AGNOSTIC_EXECUTABLE_ATTRS,
     PY_SRCS_ATTRS,
     IMPORTS_ATTRS,
+    # starlark flags attributes
+    {
+        "_build_python_zip_flag": attr.label(default = "//python/config_settings:build_python_zip"),
+        "_default_to_explicit_init_py_flag": attr.label(default = "//python/config_settings:incompatible_default_to_explicit_init_py"),
+        "_python_import_all_repositories_flag": attr.label(default = "//python/config_settings:experimental_python_import_all_repositories"),
+        "_python_path_flag": attr.label(default = "//python/config_settings:python_path"),
+    },
     {
         "interpreter_args": lambda: attrb.StringList(
             doc = """
@@ -1136,6 +1143,9 @@ def _get_runtime_details(ctx, semantics):
     # TOOD(bazelbuild/bazel#7901): Remove this once --python_path flag is removed.
 
     flag_interpreter_path = read_possibly_native_flag(ctx, "python_path")
+    if not flag_interpreter_path.startswith("python") and not paths.is_absolute(flag_interpreter_path):
+        fail("'python_path' must be an absolute path or a name to be resolved from the system PATH (e.g., 'python', 'python3').")
+
     toolchain_runtime, effective_runtime = _maybe_get_runtime_from_ctx(ctx)
     if not effective_runtime:
         # Clear these just in case
diff --git a/python/private/py_repositories.bzl b/python/private/py_repositories.bzl
index 3ad2a97214..e3ab11c561 100644
--- a/python/private/py_repositories.bzl
+++ b/python/private/py_repositories.bzl
@@ -60,10 +60,10 @@ def py_repositories(transition_settings = []):
     )
     http_archive(
         name = "bazel_skylib",
-        sha256 = "d00f1389ee20b60018e92644e0948e16e350a7707219e7a390fb0a99b6ec9262",
+        sha256 = "6e78f0e57de26801f6f564fa7c4a48dc8b36873e416257a92bbb0937eeac8446",
         urls = [
-            "https://mirror.bazel.build/github.com/bazelbuild/bazel-skylib/releases/download/1.7.0/bazel-skylib-1.7.0.tar.gz",
-            "https://github.com/bazelbuild/bazel-skylib/releases/download/1.7.0/bazel-skylib-1.7.0.tar.gz",
+            "https://mirror.bazel.build/github.com/bazelbuild/bazel-skylib/releases/download/1.8.2/bazel-skylib-1.8.2.tar.gz",
+            "https://github.com/bazelbuild/bazel-skylib/releases/download/1.8.2/bazel-skylib-1.8.2.tar.gz",
         ],
     )
     http_archive(
diff --git a/tests/base_rules/py_executable_base_tests.bzl b/tests/base_rules/py_executable_base_tests.bzl
index e86a94990a..e41bc2c022 100644
--- a/tests/base_rules/py_executable_base_tests.bzl
+++ b/tests/base_rules/py_executable_base_tests.bzl
@@ -44,7 +44,10 @@ def _test_basic_windows(name, config):
             # the target platform. For windows, it defaults to true, so force
             # it to that to match behavior when this test runs on other
             # platforms.
+            # Pass value to both native and starlark versions of the flag until
+            # the native one is removed.
             "//command_line_option:build_python_zip": "true",
+            labels.BUILD_PYTHON_ZIP: True,
             "//command_line_option:cpu": "windows_x86_64",
             "//command_line_option:crosstool_top": CROSSTOOL_TOP,
             "//command_line_option:extra_execution_platforms": [platform_targets.WINDOWS_X86_64],
@@ -87,7 +90,10 @@ def _test_basic_zip(name, config):
             # the target platform. For windows, it defaults to true, so force
             # it to that to match behavior when this test runs on other
             # platforms.
+            # Pass value to both native and starlark versions of the flag until
+            # the native one is removed.
             "//command_line_option:build_python_zip": "true",
+            labels.BUILD_PYTHON_ZIP: True,
             "//command_line_option:cpu": "linux_x86_64",
             "//command_line_option:crosstool_top": CROSSTOOL_TOP,
             "//command_line_option:extra_execution_platforms": [platform_targets.LINUX_X86_64],
diff --git a/tests/bootstrap_impls/BUILD.bazel b/tests/bootstrap_impls/BUILD.bazel
index c3d44df240..dcc27514f7 100644
--- a/tests/bootstrap_impls/BUILD.bazel
+++ b/tests/bootstrap_impls/BUILD.bazel
@@ -23,7 +23,7 @@ py_reconfig_binary(
     srcs = ["bin.py"],
     bootstrap_impl = "script",
     # Force it to not be self-executable
-    build_python_zip = "no",
+    build_python_zip = False,
     main = "bin.py",
     target_compatible_with = SUPPORTS_BOOTSTRAP_SCRIPT,
 )
@@ -50,14 +50,14 @@ sh_test(
 
 sh_py_run_test(
     name = "run_binary_zip_no_test",
-    build_python_zip = "no",
+    build_python_zip = False,
     py_src = "bin.py",
     sh_src = "run_binary_zip_no_test.sh",
 )
 
 sh_py_run_test(
     name = "run_binary_zip_yes_test",
-    build_python_zip = "yes",
+    build_python_zip = True,
     py_src = "bin.py",
     sh_src = "run_binary_zip_yes_test.sh",
 )
@@ -81,7 +81,7 @@ sh_py_run_test(
 sh_py_run_test(
     name = "run_binary_bootstrap_script_zip_yes_test",
     bootstrap_impl = "script",
-    build_python_zip = "yes",
+    build_python_zip = True,
     py_src = "bin.py",
     sh_src = "run_binary_zip_yes_test.sh",
     target_compatible_with = SUPPORTS_BOOTSTRAP_SCRIPT,
@@ -90,7 +90,7 @@ sh_py_run_test(
 sh_py_run_test(
     name = "run_binary_bootstrap_script_zip_no_test",
     bootstrap_impl = "script",
-    build_python_zip = "no",
+    build_python_zip = False,
     py_src = "bin.py",
     sh_src = "run_binary_zip_no_test.sh",
     target_compatible_with = SUPPORTS_BOOTSTRAP_SCRIPT,
diff --git a/tests/config_settings/transition/multi_version_tests.bzl b/tests/config_settings/transition/multi_version_tests.bzl
index dfe2bf9981..05f010562c 100644
--- a/tests/config_settings/transition/multi_version_tests.bzl
+++ b/tests/config_settings/transition/multi_version_tests.bzl
@@ -20,6 +20,7 @@ load("@rules_testing//lib:util.bzl", rt_util = "util")
 load("//python:py_binary.bzl", "py_binary")
 load("//python:py_info.bzl", "PyInfo")
 load("//python:py_test.bzl", "py_test")
+load("//python/private:common_labels.bzl", "labels")  # buildifier: disable=bzl-visibility
 load("//python/private:reexports.bzl", "BuiltinPyInfo")  # buildifier: disable=bzl-visibility
 load("//tests/support:support.bzl", "CC_TOOLCHAIN")
 load("//tests/support/platforms:platforms.bzl", "platform_targets")
@@ -91,7 +92,8 @@ def _setup_py_binary_windows(name, *, impl, build_python_zip):
         target = name + "_subject",
         impl = impl,
         config_settings = {
-            "//command_line_option:build_python_zip": build_python_zip,
+            "//command_line_option:build_python_zip": str(build_python_zip),
+            labels.BUILD_PYTHON_ZIP: build_python_zip,
             "//command_line_option:extra_toolchains": CC_TOOLCHAIN,
             "//command_line_option:platforms": str(platform_targets.WINDOWS_X86_64),
         },
@@ -100,7 +102,7 @@ def _setup_py_binary_windows(name, *, impl, build_python_zip):
 def _test_py_binary_windows_build_python_zip_false(name):
     _setup_py_binary_windows(
         name,
-        build_python_zip = "false",
+        build_python_zip = False,
         impl = _test_py_binary_windows_build_python_zip_false_impl,
     )
 
@@ -121,7 +123,7 @@ _tests.append(_test_py_binary_windows_build_python_zip_false)
 def _test_py_binary_windows_build_python_zip_true(name):
     _setup_py_binary_windows(
         name,
-        build_python_zip = "true",
+        build_python_zip = True,
         impl = _test_py_binary_windows_build_python_zip_true_impl,
     )
 
diff --git a/tests/integration/custom_commands_test.py b/tests/integration/custom_commands_test.py
index 2e9cb741b0..288a4e7a91 100644
--- a/tests/integration/custom_commands_test.py
+++ b/tests/integration/custom_commands_test.py
@@ -21,7 +21,7 @@
 class CustomCommandsTest(runner.TestCase):
     # Regression test for https://github.com/bazel-contrib/rules_python/issues/1840
     def test_run_build_python_zip_false(self):
-        result = self.run_bazel("run", "--build_python_zip=false", "//:bin")
+        result = self.run_bazel("run", "--build_python_zip=false", "--@rules_python//python/config_settings:build_python_zip=false", "//:bin")
         self.assert_result_matches(result, "bazel-out")
 
 
diff --git a/tests/integration/ignore_root_user_error/WORKSPACE b/tests/integration/ignore_root_user_error/WORKSPACE
index 0a25819ecd..7ac0a609eb 100644
--- a/tests/integration/ignore_root_user_error/WORKSPACE
+++ b/tests/integration/ignore_root_user_error/WORKSPACE
@@ -1,5 +1,3 @@
-load("@bazel_tools//tools/build_defs/repo:http.bzl", "http_archive")
-
 local_repository(
     name = "rules_python",
     path = "../../..",
@@ -14,16 +12,3 @@ python_register_toolchains(
     ignore_root_user_error = True,
     python_version = "3.9",
 )
-
-http_archive(
-    name = "bazel_skylib",
-    sha256 = "c6966ec828da198c5d9adbaa94c05e3a1c7f21bd012a0b29ba8ddbccb2c93b0d",
-    urls = [
-        "https://mirror.bazel.build/github.com/bazelbuild/bazel-skylib/releases/download/1.1.1/bazel-skylib-1.1.1.tar.gz",
-        "https://github.com/bazelbuild/bazel-skylib/releases/download/1.1.1/bazel-skylib-1.1.1.tar.gz",
-    ],
-)
-
-load("@bazel_skylib//:workspace.bzl", "bazel_skylib_workspace")
-
-bazel_skylib_workspace()
diff --git a/tests/support/py_reconfig.bzl b/tests/support/py_reconfig.bzl
index d52cc5dd95..efcb0e7a38 100644
--- a/tests/support/py_reconfig.bzl
+++ b/tests/support/py_reconfig.bzl
@@ -17,6 +17,7 @@ This facilitates verify running binaries with different configuration settings
 without the overhead of a bazel-in-bazel integration test.
 """
 
+load("@rules_python_internal//:rules_python_config.bzl", "config")
 load("//python/private:attr_builders.bzl", "attrb")  # buildifier: disable=bzl-visibility
 load("//python/private:common_labels.bzl", "labels")  # buildifier: disable=bzl-visibility
 load("//python/private:py_binary_macro.bzl", "py_binary_macro")  # buildifier: disable=bzl-visibility
@@ -30,7 +31,8 @@ def _perform_transition_impl(input_settings, attr, base_impl):
     settings.update(base_impl(input_settings, attr))
 
     settings[labels.VISIBLE_FOR_TESTING] = True
-    settings["//command_line_option:build_python_zip"] = attr.build_python_zip
+    settings["//command_line_option:build_python_zip"] = str(attr.build_python_zip)
+    settings[labels.BUILD_PYTHON_ZIP] = attr.build_python_zip
     if attr.bootstrap_impl:
         settings[labels.BOOTSTRAP_IMPL] = attr.bootstrap_impl
     if attr.extra_toolchains:
@@ -58,13 +60,14 @@ _RECONFIG_INPUTS = [
 ]
 _RECONFIG_OUTPUTS = _RECONFIG_INPUTS + [
     "//command_line_option:build_python_zip",
+    labels.BUILD_PYTHON_ZIP,
     labels.VISIBLE_FOR_TESTING,
 ]
 _RECONFIG_INHERITED_OUTPUTS = [v for v in _RECONFIG_OUTPUTS if v in _RECONFIG_INPUTS]
 
 _RECONFIG_ATTRS = {
     "bootstrap_impl": attrb.String(),
-    "build_python_zip": attrb.String(default = "auto"),
+    "build_python_zip": attrb.Bool(default = config.build_python_zip_default),
     "config_settings": attrb.LabelKeyedStringDict(),
     "extra_toolchains": attrb.StringList(
         doc = """